How to Ask Out a Shy Guy in High School

Written by John Keegan | Edited by Megaera Lorenz, PhD

Last Updated: December 2, 2022 References

Having a crush on a shy guy can be frustrating, especially if you’re used to waiting for him to make the first move. It takes a bit of courage to ask any guy out, but with a little patience, you can totally do it. In this article, we’ll talk you through how to ask your shy crush out—and get him out of his shell.

This article is based on an interview with our professional dating coach, John Keegan, founder of The Awakened Lifestyle. Check out the full interview here.

Method 1

Method 1 of 3:

Making Your Move

1
Ask him out directly. When you’re ready to make your move, get right to the point. Stay chill and keep it light and friendly. Say something like, “Wanna hang out later?” or “I really like you. Will you go see a movie with me this weekend?”^{[1]
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- Pick a time when he’s not too busy or distracted. For example, you might come up to him during lunch or after classes are over.
- If he’s too nervous to answer right away, give him some space. Say something like, “No rush, just let me know!” Write down your number or email address for him so he can get back to you.
2
Invite him out over text for less pressure. If you’re too nervous to ask him face-to-face, send him a text or email. That’ll also take the pressure off him to answer right away and give him time to think about his response.
- Say something like, “I always enjoy seeing you in STEM club. Want to hang out sometime? I’m free this Friday after school.”
- If you’re not comfortable just asking out of the blue, lead up to it by starting a conversation about something else. For example, text something like, “Wow, that chemistry test was crazy! What did you think of question 3?” If it seems like he’s enjoying the chat, go ahead and take the plunge!
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3
Go old-school and slip him a note. Writing a note is a cute, old-fashioned way of asking out your crush—and it’s also lower pressure than having a face-to-face chat. Write down your number in a card or on a slip of paper, and add a message like “Want to go out with me? :)” or “I think you’re awesome. Let’s hang out.”^{[2]
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- You can hand the note to him directly, or do something a little sneakier, like slipping it onto his desk when he’s not looking.
4
Ask him for help if you don’t want to be direct. It’s always flattering when someone asks you for help. It’s also a good way to break the ice and lead up to asking him out on an official date, if you’re not quite ready to make that step.^{[3]
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- For instance, you might say, “I’ve been struggling with this creative writing assignment, but you seem really good at this stuff. Want to get together after school today and brainstorm some ideas?”
- If it goes well, take the excuse to ask him out for an actual date. Say something like, “It was really cool hanging out with you. We should do it again sometime, just for fun! Would you want to do something this weekend?”
5
Respect his wishes if he says no. Rejection can be a huge bummer, but it’s important not to keep putting the pressure on him if he’s not interested. Let him know how you feel, then back off. Don’t keep asking him if he says “no.”^{[4]
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- If he’s really shy, he might have a hard time giving you a clear answer right away, even if he is interested. If he needs time to think about it, leave him alone and give him some time and space to respond.

Method 2

Method 2 of 3:

Going Out

1
Ask him to do an activity with you. A lot of shy dudes dread having to make small talk. Instead of just going out for dinner or coffee, invite him to go someplace where you can do something together. That will take the pressure off him to make conversation and help him feel more at ease.^{[5]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 29 June 2021.}
- For instance, you could invite him to go to a game night with you, take him to a show or concert, or take him to your favorite stargazing spot.
2
Go someplace where he feels comfortable. Think about what your special guy is into and what he’s good at. He’s more likely to come out of his shell if you go someplace where he feels at home and can let his strengths shine.^{[6]
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- For instance, if he’s a sports fan, you could invite him to watch a game with you. Or, if he’s a gamer, you could go to an arcade together.
3
Ask him some open-ended questions. If he’s having a hard time opening up while you’re together, asking questions can be a good way to keep the conversation flowing. Ask questions that he’ll need to use more than 1 or 2 words to answer!^{[7]
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- For instance, avoid “yes” or “no” questions. Instead, ask him things like, “What’s your favorite class this year?” or “What do you think is going to happen in the next season of ‘Stranger Things’?”
- If you’re not sure what to ask, try some classic ice-breaker questions. For example, “What’s a random fun fact about you?” “What’s your favorite joke?” or, “What’s your favorite place in the world?”^{[8]
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4
Talk about a common interest. If there’s anything you’re both into, talking about it can be a great way to bond and help him feel more at ease. Let him know you share his interest, and ask him questions to get him talking about it.^{[9]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 29 June 2021.}
- For instance, you could say, “It’s so cool that you’re into anime, too! What’s your favorite show?”
- If you don’t know what he likes, ask him questions to try and find out. For example, ask him things like, “What shows do you like to watch?” “Who’s your favorite author?” or, “Do you have any hobbies?”
5
Try some light touches if he seems into you. Even if he’s really into you, a shy guy can have a hard time working up the courage to get physical. Instead of waiting for him to make a move, try putting your hand on his arm, leaning on his shoulder, or taking his hand. If it seems like he’s into it, you can even go in for a hug or a kiss.^{[10]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 29 June 2021.}
- Physical touch can be a big confidence booster for a guy who’s not too sure of himself. If you make the first move—for example, by brushing your hand against his—he might feel brave enough to take the next step himself.
- You can also break the touch barrier in a more fun, lighthearted way. For example, ask him to thumb-wrestle you or offer to read his palm.
6
Give him time and space to open up. It can be frustrating to date someone who’s shy or introverted, but try to be patient. It’ll probably take some time for him to relax and come out of his shell. Be chill, take it slow, and try to enjoy the process of getting to know him.^{[11]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 29 June 2021.}
- Avoid putting pressure on him to open up or be talkative. Just relax and enjoy being with him in those quiet moments when neither one of you is sure what to say.
- Try to match his energy when you’re together. For instance, if he’s in a quiet mood, don’t worry too much about trying to fill the silence or keep the conversation going.
7
Avoid mentioning his shyness. People who are shy tend to be self-conscious about a lot of things—including being shy! Don’t put him on the spot by bringing up how quiet or introverted he is, even if it’s something you like about him.^{[12]
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Method 3

Method 3 of 3:

Breaking the Ice

1
Check for signs that he’s into you. It can be hard to tell if that quiet, reserved guy is interested in you. For one thing, even if he has a huge crush on you, he’s probably too shy to say so! Before you make your move, pay attention to the little signs that he feels the same way you do. For instance:^{[13]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 29 June 2021.}
- You might catch him staring or stealing quick glances at you, then quickly looking away when you notice.
- He may act unusually nervous or tongue-tied around you.
- He might look for excuses to hang around you, even if he doesn’t really talk to you much.
- You may spot body language that show’s he’s into you—for instance, he might blush or fiddle with his hair a lot when you’re interacting with him.
2
Make eye contact with him. Next time you see your shy guy, look at him and smile. Locking eyes is a great way to show you’re into him and want to get to know him better!^{[14]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 29 June 2021.}
- Don’t get discouraged if he has trouble returning your gaze. Making eye contact can be tough for people who are less outgoing.
3
Call him by name when you talk to him. When you use a guy’s name, it lets him know he’s important to you. Look for ways to casually drop his name into the convo next time you chat.^{[15]
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- For example, say something like, “What did you think of that quiz in English yesterday, Jacob?”
- You could also try calling him by a cute nickname—just make sure it’s a nice one and not something that could hurt his feelings. For instance, if he’s really good at photography, you could say, “Hey, how’s it going, Shutterbug?”
4
Joke around with him in a flirty way. A bit of friendly teasing or joking can help put a shy guy at ease and let him know you like him. Just keep it light and avoid anything that might sound mean-spirited or make him self-conscious.^{[16]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 29 June 2021.}
- Smile and keep your tone friendly so he knows you’re joking around—especially if you’re teasing him.
- For example, you could say something like, “Wait, you’re good looking, smart, and creative? No fair, dude.”
- Not all your humor has to be about him. You can also crack a corny joke, tell a funny story, poke a little fun at yourself, or just cut loose and be silly around him.^{[17]
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5
Give him an honest compliment. A sincere compliment will help boost your crush’s self-esteem, and it’s also a clear signal that you like him. Be specific and genuine—comment on something you actually admire about him instead of making it something vague, like “You look nice,” or “You seem cool.”^{[18]
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- For example, say something like, “That shirt is awesome, where did you get it?” or, “You really killed it in drama club yesterday, that monologue was amazing!”
- Be careful about commenting on his looks, since that can make some shy people uncomfortable.
6
Send him a fun, low-pressure text. A lot of shy guys are more comfortable talking online or over text than face to face. If you have his number already, shooting him a friendly text can be a good way to start a conversation and lead up to asking him out.^{[19]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 29 June 2021.} If you don’t already have his digits, look for an excuse to ask. Say something like, “I’m putting together a study group, and I wanted to add you to the list. Can I get your number?”
- You could just say “Hi,” tell him a joke, or send him an interesting image or link. For instance, if you know he likes a particular band, send him a link to one of their music videos. Say something like, “I was watching this earlier and I thought of you!”
- You could also get a convo going by asking him a question. For example, say something like, “Have you had a chance to start that assignment for biology yet?”
- If he opens up and starts chatting, let it lead naturally into asking him out. For instance, say something like, “It’s so much fun talking to you. Want to hang out in person sometime?”